Long Island is often thought of as a summer playground for wealthy urbanites from New York and, being so close to the city, it’s easy to understand why this might have become the case. Today, it’s not just New Yorkers who flood here ‘to summer’ on beautiful Long Island beaches and hang out in the smart Hamptons and dreamy vineyards. We passed through on our short road trip loop and would return in a heartbeat. Read on to find out why…
Where is Long Island?
Long Island in New York state stretches east from New York City for around 190 km (120 miles), with John F. Kennedy Airport to the west and Montauk to the east, the New York Sound running long its northern edge, Block Island Sound to the right and Atlantic Ocean on its southern side.
Long Island is therefore perfectly accessible from John F. Kennedy Airport, and from a road trip perspective, you can be out of the airport and straight onto the Long Island roads without having to navigate New York City. Check out my blog about Travel Planning a Road Trip from Long Island for more information about the roads (and ferry crossings).
There are many beautiful sandy Long Island beaches very close to Manhattan, including Jones Beach which is only 40 miles from Midtown Manhattan, making it Long Island’s most famous and accessible stretch of sand.
The Hamptons
The Hamptons is a collection of towns and villages across the South fork of Long Island, including Westhampton (the original Hampton), Southampton, East Hampton, Amagansett, Montauk, Sag Harbor** and several more. **Using American spellings for place names – Sag Harbor / Montauk Harbor
As a guide, the drive from JFK Airport to Montauk at the furthest point east takes around 2 hours 50 minutes, or 1 hour 50 minutes to Westhampton.
When to go?
High Season for this the Hamptons is from the end of May until the start of September. During this time, everything will be open and ready for beach life with summer activities on the Long Island beaches.
Many of the Long Island beaches are private but that said, there are still plenty of stunning public beaches to explore. Note – in some areas you may require beach passes (or parking permits) for High Season visits, but your accommodation may be able to help you with these.
We were travelling in the third week of July and had beautiful weather on all but one morning, when there was a thunderstorm which passed by early afternoon.
Southampton, a good base in the Hamptons
As we were exploring the area on a road trip, we weren’t too bothered about booking somewhere with beach access, so settled on a guest house in Southampton through Booking.com. Whilst its location was good, I wouldn’t particularly recommend the guest house due to its creaky floorboards, noisy adjoining restaurant, and surly staff.
However, I spotted the nearby 1708 House which, from its website, looked like a much better option right in the town centre. This was also available on Booking.com and includes Southampton beach passes in their prices. I’ve made a mental note of this one, should there be a next time!
What to expect in Southampton
Southampton is a well-heeled town with smart shops and buzzing restaurants set out around a crossroads, keeping everything close together. Whilst the town has a relatively slow pace of life, you can find:
- History – note the old street sign showing the town’s age, year 1648.
- Cute buildings – the Pelletreu Silver Shop, a tiny Dutch barn made in 1688, once the workshop of a Silversmith from 1726-1810. Also note the pretty white clapboard buildings and churches, such as, the Methodist and First Presbyterian Churches.
- Compact shopping – there is a nice mix of brand shopping such as J Crew and Ralph Lauren, plus lots of independent shops and boutiques, all in a couple of small streets.
- Gourmet food markets and delis – Citarella is a gourmet market (posh supermarket) selling things which are perfect for picnics, plus hot options and lots of snacks. I’ve never come across as many organic delis in one square mile before!
- Wellness outlets – for beauty and spa treatments, including Hampton Hot Yoga.
- Beautiful beaches – an array of golden sandy beaches (see below).
Although we didn’t eat out much in Southampton due to our schedule, the restaurants looked busy, such as 75 Main (apparently a celeb haunt) and Argent. The Golden Pear was good picking up coffees, pastries, bagels, and Hampton-themed sandwiches. After paying, you can pour your own coffee from the hot plates on the counter which feels very American.
Buddhaberrry is a great frozen yoghurt outlet when you can ‘try before you buy’ from a large assortment of flavours before adding from a multitude of toppings.
We enjoyed Happy Hour cocktails and beers at the Southampton Publick House one night, sitting in the outdoor patio with one eye on the baseball on the TV screens and one eye on the comings and goings around us.
Southampton looked pretty at night, lit up by fairy lights, and with fireflies visible in the grassy areas!
Chill on Cooper’s Beach
My pre-trip research of the Long Island beaches suggested that Cooper’s Beach was “one of the best public beaches” in the Hamptons, so we bought sushi from Citarella and headed over to the beach for 6pm by which time parking was free and permits weren’t required.
Cooper’s Beach is a wide stretch of soft, golden sand with Atlantic rollers in front and huge houses backing onto the sand, with lifeguards on duty during the day (see featured photo).
During the summer season, there’s a programme of live music on the beach, so we were able to chill out on the beach along with locals and holiday makers, sharing wine, chatting, and listening to the music. Whilst jet lag cut our evening short, we still felt that we had experienced a slice of real Hamptons life in the fading sunlight of a summer’s evening.
If rubber-necking enormous houses is your thing, then you can check out the whoppers on Gin Lane in Southampton, home to some of the most expensive pads on Long Island (reportedly up to $150 million – fact check required). We took a detour down Billionaire’s Lane (Meadow Lane) to ogle at the multi-million-dollar homes and spotted a deer strolling casually down one of the driveways – welcome to the Hamptons!
Explore more of the Hamptons
Our strategy was to drive to the furthest point and work our way back to Southampton, so we headed over to Montauk State Park at the eastern most point (‘the End’), where Block Island Sound meets the Atlantic Ocean, just over one hours’ drive from Southampton.
Montauk Point State Parks
There are six state parks in Montauk, including: Montauk Point State Park, Camp Hero, Montauk Downs, Hither Hills, Shadmoor, and Napeague, all offering places to explore and go for walks in the wild landscape. Cape Hero has an historic military installation to see as well as forest, beaches, and fabulous ocean views.
Montauk Point Lighthouse
The Montauk Point Lighthouse sits next to Montauk Point State Park at ‘the End’ and is the oldest lighthouse in New York state, commissioned by President George Washington in 1792. Before the English settlers and development of the lighthouse, Algonquin-speaking Montaukett Indians would light watch fires on the cliffs here to guide their canoes home.
There’s a large car park at the lighthouse which opens at 10.30am until 4.30pm daily (longer on Sundays). It costs $15 entry per person to access the lighthouse and a small museum.
Enter the lighthouse keeper’s house and explore the exhibits of the ground floor museum, which explain the history and significance of this historic lighthouse. On the displays, look out for:
- The documents written and signed by George Washington and Thomas Jefferson.
- The story of Princess Pocahontas Pharoah, the daughter to David and Maria Pharoah, King and Queen of the Montauk tribe. Princess Pocahontas was known for making medicines from herbs and shrubs.
- The photo of Frank Mundus, a local shark fisherman said to be the inspiration for the character Quint in the film JAWS, filmed in nearby Martha’s Vineyard.
Then climb the 137 steps to the watch deck of this still working lighthouse to see the large lens at the top and views over the water, staying alert for signs of Abigail the ghost of the lighthouse.
Back at ground level, take a moment to remember those Lost at Sea at the memorial on the cliff edge.
Montauk Harbor
Head west towards Montauk before taking the turning towards Montauk Downs State Park and Montauk Harbor. Wander around this nautical area, home to the largest fishing fleet in New England and Gosman’s Fish Market.
If it’s lunchtime and you’re hungry, pick up a Lobster Roll or Lobster Bisque from Gosman’s Clam Bar and sit at one of the outdoor tables watching the boats coming and going from Lake Montauk and Block Island Sound. Watch out for the greedy seagulls!
If you want to explore more of the wonderful Long Island beaches then there are plenty around Montauk, including Ditch Plains Beach (with surfing opportunities) and family friendly Gin Beach.
We didn’t stop in Montauk Village choosing instead deciding to continue to East Hampton. If you didn’t eat in Montauk Harbor, then you might consider stopping at LUNCH Lobster Roll in Amagansett on the way, known for its lobster rolls made of 100% pure cold-water lobster. Look out for local resident Gwyneth Paltrow whilst in Amagansett!
Window shop in East Hampton
On the way in and out of East Hampton you pass the Hook Windmill, a wonderful old windmill built in 1806 which operated for 100 years turning grain into flour and feed – one of 11 windmills on Long Island.
The town of East Hampton has the glitziest shops, including luxury brands such as Luis Vuitton, Chanel, and Prada. It also seemed to have the most traffic and impatient drivers honking their horns!
We enjoyed some window shopping in this exclusive town, browsing in the book shop, before picking up snacks from Citarellas (when something works…) before heading off to the Longhouse Reserve in search of some solitude.
Visit Longhouse Reserve – hidden gem in the Hamptons
The Longhouse Reserve sculpture park is a don’t miss destination if you have time to wander through the 16 acres of pretty gardens and trees. It’s the home of late textile artist Jack Lenor Larsen and the gardens are full of sculptures by well-known artists, such as Yoko Ono, Wilem de Kooning, Ai Wei Wei, and Daniel Arsham, although the pieces on display change periodically.
When it’s hot in the Summer, this is the perfect place to seek sanctuary under the shade of the trees. I loved Dale Chihuly’s Cobalt Reeds by the lake, having been a fan of his art since we visited his glass museum in Seattle. I also enjoyed spotting the tame rabbits bobbing around the grounds.
If you like art and have the time, you can also visit the Pollack-Krasner House – former home and studio of Jackson Pollock and Lee Krasner which is nearby.
Don’t miss Sag Harbor
Sag Harbor is about 30 minutes’ drive northeast of Southampton and was my favourite place in the Hamptons (despite its extensive whaling history). It was once home to Algonquin Indians which linked with a previous canoeing adventure in Algonquin Park, Ontario, Canada.
First, we explored the windmill standing at the entrance to Long Wharf filled with lovely boats of various shapes and sizes. The original windmill was built in 1760 to be used in the processing of whale oil during the 19th century. The one you see today is a replica, erected as an historic monument to the whaling industry which once made Sag Harbor a bustling, commercial port town. We gave the Whaling Museum a miss…
Despite its small size, Sag Harbor has both a small Art Deco cinema and the Bay Street Theatre, along with a lively main street of shops, antique stores, and restaurants. The town also has a BuddhaBerry Frozen Yoghurt shop – noted!
If you have an opportunity to stay over for a night then consider the upmarket American Hotel, or alternatively book in for a meal (reservations generally required).
John Steinbeck’s House
John and Elaine Steinbeck lived in Sag Harbor from 1955 until his death in 1968, and is now open for visits. He wrote The Winter of Our Discontent during his time living at the house.
When we visited I was reading Travels with Charley by Steinbeck which follows his road trip in search of the real America. Charley is his French Poodle who dog lovers with adore. His journey sets out from Sag Harbor and takes the same ferry routes (detailed below) across to New London, Connecticut. I didn’t realise we would be following in his footsteps when planning our route!
Take the South Ferry to Shelter Island for lunch
As explained in my blog Travel Planning a Long Island Road Trip, you can take a small car ferry across the water to Shelter Island, only 5 minutes away.
We took the ferry across and enjoyed a lovely lunch at SALT Waterfront Bar and Grill on the deck overlooking a small marina with the Peconic Bay in the background.
Take the North Ferry to Greenport
After lunch, and potentially a snooze on Crescent Beach on the northwest of Shelter Island (more pebbly than most of the Long Island beaches), you can then catch the North Ferry to Greenport on the north fork of Long Island.
North fork vineyards
We decided to stay for a night in Greenport to be well positioned to visit some of the many vineyards in this area, including:
- La Croteaux – a French styled (Provence) tasting garden and winery specializing in Rosé wines. It’s open from 11am to 6pm and you can pop in, no reservations required, to sample a flight of rosé whilst sitting in an idyllic garden next to the vines.
- McCall Wines – we booked a special Burger and Wine Night at McCalls and spent a wonderful couple of hours sitting in a garden lit by fairy lights outside a barn, sampling red wines. You should book a slot for this special event as all tables were full for the duration of our visit. I loved watching groups of friends and multi-generational families chatting and eating as the sun started to set.
Note 1 – most accommodation options in the north fork seemed to have minimum night stays and I concluded that it is a very popular spot, not just with New Yorkers and locals, but also with visitors from New England coming via the Connecticut ferry. It would make the perfect weekend getaway from across the water!
Note 2 – there are also vineyards in the South fork including: Duck Walk Vineyard, Wolffer Estate Vineyard, and the Channing Draught Winery. If we hadn’t been intending to catch the ferry to Connecticut from the north fork of Long Island, then we might have stayed longer in the South fork and explored the vineyards there.
Final thoughts….
Long Island made for an enjoyable destination and one which I would be happy to return to.
I’m not sure we found the heart of Montauk and so I would be keen to try again there, but Sag Harbor was a destination of choice.
The whole area was spotless, easy to drive around and very pretty – tick!
There’s no escaping the fact that the area is pricey, even if you’re only in town for a couple of days but sharing food (as portion sizes so generous) and staying in guest houses helped to keep our costs down a bit. Our ‘summer playground’ was the public beach rather than the private beach clubs, but that’s fine with us. Just happy to be in town!
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